WO2000061537A2 - Pharmaceutical compounds - Google Patents
Pharmaceutical compounds Download PDFInfo
- Publication number
- WO2000061537A2 WO2000061537A2 PCT/EP2000/003234 EP0003234W WO0061537A2 WO 2000061537 A2 WO2000061537 A2 WO 2000061537A2 EP 0003234 W EP0003234 W EP 0003234W WO 0061537 A2 WO0061537 A2 WO 0061537A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- thε
- drugs
- drug
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 153
- 229940079593 drug Drugs 0.000 claims abstract description 200
- 239000003814 drug Substances 0.000 claims abstract description 200
- 239000002243 precursor Substances 0.000 claims abstract description 103
- 238000012360 testing method Methods 0.000 claims abstract description 69
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- -1 isopropyl ester Chemical class 0.000 claims description 219
- 239000000243 solution Substances 0.000 claims description 77
- 239000002253 acid Substances 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 39
- 230000002496 gastric effect Effects 0.000 claims description 37
- KCWZGJVSDFYRIX-YFKPBYRVSA-N N(gamma)-nitro-L-arginine methyl ester Chemical compound COC(=O)[C@@H](N)CCCN=C(N)N[N+]([O-])=O KCWZGJVSDFYRIX-YFKPBYRVSA-N 0.000 claims description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 230000006378 damage Effects 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 28
- 241000700159 Rattus Species 0.000 claims description 27
- 150000003254 radicals Chemical class 0.000 claims description 25
- 229960000905 indomethacin Drugs 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 20
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 18
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 claims description 17
- 108010082126 Alanine transaminase Proteins 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims description 15
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 15
- 235000001785 ferulic acid Nutrition 0.000 claims description 15
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 15
- 229940114124 ferulic acid Drugs 0.000 claims description 15
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 15
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims description 15
- 230000005764 inhibitory process Effects 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 231100000419 toxicity Toxicity 0.000 claims description 14
- 230000001988 toxicity Effects 0.000 claims description 14
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 13
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 12
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 229940083542 sodium Drugs 0.000 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- 230000036772 blood pressure Effects 0.000 claims description 11
- 229960005489 paracetamol Drugs 0.000 claims description 11
- 206010067125 Liver injury Diseases 0.000 claims description 10
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 10
- 229960005174 ambroxol Drugs 0.000 claims description 10
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 claims description 10
- 230000001713 cholinergic effect Effects 0.000 claims description 10
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 10
- 231100000234 hepatic damage Toxicity 0.000 claims description 10
- 230000008818 liver damage Effects 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229960004150 aciclovir Drugs 0.000 claims description 9
- 230000006907 apoptotic process Effects 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229920000669 heparin Polymers 0.000 claims description 9
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 9
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 8
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 8
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 8
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 8
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 8
- 239000003472 antidiabetic agent Substances 0.000 claims description 8
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 8
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 8
- 229960002052 salbutamol Drugs 0.000 claims description 8
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 claims description 8
- 229960001685 tacrine Drugs 0.000 claims description 8
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 8
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 claims description 7
- 108010061435 Enalapril Proteins 0.000 claims description 7
- 238000002835 absorbance Methods 0.000 claims description 7
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 7
- 239000008280 blood Substances 0.000 claims description 7
- 210000004369 blood Anatomy 0.000 claims description 7
- 229940124630 bronchodilator Drugs 0.000 claims description 7
- 239000000168 bronchodilator agent Substances 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 7
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 claims description 7
- 229960000873 enalapril Drugs 0.000 claims description 7
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000001727 in vivo Methods 0.000 claims description 7
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 claims description 7
- 229960005249 misoprostol Drugs 0.000 claims description 7
- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 claims description 7
- 229960000381 omeprazole Drugs 0.000 claims description 7
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003047 N-acetyl group Chemical group 0.000 claims description 6
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 6
- 230000003266 anti-allergic effect Effects 0.000 claims description 6
- 230000002785 anti-thrombosis Effects 0.000 claims description 6
- 239000003146 anticoagulant agent Substances 0.000 claims description 6
- 239000002876 beta blocker Substances 0.000 claims description 6
- 229940097320 beta blocking agent Drugs 0.000 claims description 6
- 230000005779 cell damage Effects 0.000 claims description 6
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 6
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims description 6
- 229960003009 clopidogrel Drugs 0.000 claims description 6
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims description 6
- 229960004679 doxorubicin Drugs 0.000 claims description 6
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 6
- 229960005219 gentisic acid Drugs 0.000 claims description 6
- 229960001867 guaiacol Drugs 0.000 claims description 6
- 229960001680 ibuprofen Drugs 0.000 claims description 6
- VDVJGIYXDVPQLP-UHFFFAOYSA-N piperonylic acid Chemical compound OC(=O)C1=CC=C2OCOC2=C1 VDVJGIYXDVPQLP-UHFFFAOYSA-N 0.000 claims description 6
- 229960002702 piroxicam Drugs 0.000 claims description 6
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 6
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims description 5
- 239000005541 ACE inhibitor Substances 0.000 claims description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 5
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 5
- 229960000723 ampicillin Drugs 0.000 claims description 5
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 229940127003 anti-diabetic drug Drugs 0.000 claims description 5
- 230000000259 anti-tumor effect Effects 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 5
- 239000003443 antiviral agent Substances 0.000 claims description 5
- 230000003115 biocidal effect Effects 0.000 claims description 5
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 claims description 5
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 5
- 229960002768 dipyridamole Drugs 0.000 claims description 5
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003651 drinking water Substances 0.000 claims description 5
- 235000020188 drinking water Nutrition 0.000 claims description 5
- 230000003511 endothelial effect Effects 0.000 claims description 5
- 229960002390 flurbiprofen Drugs 0.000 claims description 5
- 150000001261 hydroxy acids Chemical class 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 229940066491 mucolytics Drugs 0.000 claims description 5
- 229960003966 nicotinamide Drugs 0.000 claims description 5
- 235000005152 nicotinamide Nutrition 0.000 claims description 5
- 239000011570 nicotinamide Substances 0.000 claims description 5
- 229960002508 pindolol Drugs 0.000 claims description 5
- 229960002855 simvastatin Drugs 0.000 claims description 5
- 239000012085 test solution Substances 0.000 claims description 5
- 229960004605 timolol Drugs 0.000 claims description 5
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 4
- RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 claims description 4
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 4
- CRTGSPPMTACQBL-UHFFFAOYSA-N 2,3-dihydroxycyclopent-2-en-1-one Chemical compound OC1=C(O)C(=O)CC1 CRTGSPPMTACQBL-UHFFFAOYSA-N 0.000 claims description 4
- XVDXNSRMHBAVAX-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-propan-2-ylbenzo[e]benzimidazole Chemical compound C1=CC(OC)=CC=C1C(N1C(C)C)=NC2=C1C=CC1=CC=CC=C21 XVDXNSRMHBAVAX-UHFFFAOYSA-N 0.000 claims description 4
- LVYLCBNXHHHPSB-UHFFFAOYSA-N 2-hydroxyethyl salicylate Chemical compound OCCOC(=O)C1=CC=CC=C1O LVYLCBNXHHHPSB-UHFFFAOYSA-N 0.000 claims description 4
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 claims description 4
- DZAUWHJDUNRCTF-UHFFFAOYSA-N 3-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(O)C(O)=C1 DZAUWHJDUNRCTF-UHFFFAOYSA-N 0.000 claims description 4
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims description 4
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 claims description 4
- NWPRCRWQMGIBOT-UHFFFAOYSA-N 7-(2-hydroxyethyl)-1,3-dimethylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CCO)C=N2 NWPRCRWQMGIBOT-UHFFFAOYSA-N 0.000 claims description 4
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 4
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims description 4
- MROJXXOCABQVEF-UHFFFAOYSA-N Actarit Chemical compound CC(=O)NC1=CC=C(CC(O)=O)C=C1 MROJXXOCABQVEF-UHFFFAOYSA-N 0.000 claims description 4
- WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 4
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 claims description 4
- 239000002083 C09CA01 - Losartan Substances 0.000 claims description 4
- 229930188120 Carbomycin Natural products 0.000 claims description 4
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/18—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/48—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C07C327/34—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups with amino groups bound to the same hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
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- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
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- C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
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- C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines
Definitions
- the present invention relates to novel drugs for systemic use and non systemic use, and the composition thereof, to be used in oxidative stress and/or endothelial dysfuntions cases.
- oxidative stress it is meant the generation of free radicals or radicalic compounds, which causes injury both of the cell and that of the surrounding tissue (Pathophysiology: the biological basis for disease in adults and children, McCance & Huether 1998 pages 48-54).
- endothelial dysfunctions those relating to the vasal endothelium.
- the damage of the vasal endothelium is known as one of those important events that can cause a series of pathological processes affecting various organs and body apparatuses, as described hereinafter (Pathophysiology: The biological basis for disease in adults and children, McCance & Huether 1998 page 1025).
- the oxidative stress and/or the endothelial dysfunctions are associated to various pathologies as reported hereinafter.
- the oxidative stress can also be caused by toxicity of a great variety of drugs, which significantly affects their performances. Said pathological events are of a chronic, debilitating character and are very often typical of the elderly . As already said, in said pathological conditions the drugs used show a remarkably worsened performance.
- pathological situations caused by the oxidative stress and/or by the endothelial dysfunctions, or present in elderly are the following:
- cardiovascular system myocardial and vascular ischaemia in general, hypertension, stroke, arteriosclerosis, etc.
- ulcerative and non ul- cerative dyspepsias ulcerative and non ul- cerative dyspepsias, intestinal inflammatory diseases, etc.
- Drug research is directed to find new molecules having an improved therapeutic index ( efficacy/toxicity ratio) or a lower risk/benefit ratio, also for pathological conditions as those above mentioned, wherein the therapeutic index of a great number of drugs results lowered.
- therapeutic index efficacy/toxicity ratio
- a lower risk/benefit ratio also for pathological conditions as those above mentioned, wherein the therapeutic index of a great number of drugs results lowered.
- many drugs show a lower activity and/or higher toxicity.
- NSAIDs result toxic particularly when the organism is debilitated or affected by morbid conditions associated to oxidative stress. Said conditions are for example the following: age, pre-existing ulcer, pre-existing gastric bleeding, debilitating chronic diseases such as in particular those affecting cardiovascular, renal apparatuses, the haematic crasis, etc.
- Mcisoprostol reduces serious gastrointestinal complications in patients with rheumatoid arthritis receiving non- steroidal anti - inflammatory drugs. A randomized, double blind, placebo-controlled trial.”
- F.E. Silverstein et Al . Ann. Intern. Med. 123/4, 241-9, 1995; Martindale 31a e ⁇ . 1996, pag . 73, Current Medical Diagnosis and Treatment 1998, pages 431 and 794).
- Beta-blockers used for the angina, hypertension and cardiac arrhythmia treatment, show side effects towards the respiratory apparatus (dyspnoea, bronchoconstriction) , and therefore they can cause problems in patients affected by pathologies to said organs (asthma, bronchitis). Therefore beta-blockers further worsen respiratory diseases such as asthma. Therefore in asthmatic patients reduced doses of said drugs must be used in order not to jeopardize even more the respiratory functionality. Thus the efficacy of the beta-blockers results very reduced.
- Antithrombotics such as for example dipyridamole , aspirin, etc., used for the prophylaxis of thrombotic phenomena, have the same drawbacks.
- the therapeutic action or the tolerability of these drugs, as in the case of aspirin is greatly reduced.
- Bronchodilators for example salbutamol, etc. are used in the asthma and bronchitis treatment and drugs active on the cholinergic system are used in pathologies such as urinary cholinergic incontinence. Their administration can produce similar side effects affecting the cardiovascular apparatus, causing problems both to cardiopathic and to hypertensive patients. Cardiopathies and hypertension are pathologies associated, as above said, to the oxidative stress and/or endothelial dysfunctions. Also these drugs show the same drawbacks as those above mentioned.
- Expectorant and ucolytic drugs which are used in the therapy of inflammatory states of the respiratory organs, show drawbacks in patients affected by the above described conditions. Their administration can give rise to heartburn and gastric irritability, particularly in the elderly.
- Bone resorption inhibitors such as diphosphonates (for example alendronate, etc.) are drugs showing high gastrointestinal toxicity. Therefore also these drugs can show the same drawbacks as those above mentioned.
- Phosphodiesterase inhibitors such as for example sildenafil, zaprinast , used in the cardiovascular and respiratory system diseases, are charaterized by similar problems as to tolerability and/or efficacy in the mentioned pathological conditions of oxidative stress and/or endothelial dy ⁇ funtions .
- Antiallergic drugs for example cetirizine, montelukast, etc. show similar problems in the mentioned pathological conditions, particularly for that it concerns their efficacy.
- Anti-angiotensin drugs f.i. ACE- inhibitors , for example enalapril, captopril, etc., and receptor inhibitors, for example losartan, etc.
- Their drawback is to give side effects to the respiratory apparatus (i.e. cough, etc.) in the above mentioned pathological conditions.
- Antidiabetic drugs both of the insulin- sensitizing and of hypoglycaemizing type, such as for example sulphonylureas , tolbutamide , glypiride, glyclazide, glyburide, nicotinamide etc., are ineffective in the prophylaxis of diabetic complications. Their administration can give side effects, such as for example gastric lesions. These phenomena become more intense in the pathological conditions above mentioned.
- Antibiotics for example ampicillin, clarihtromycin, etc., and antiviral drugs, acyclovir, etc., show problems as regards their tolerability, for example they cause gastro- intestinal irritability.
- Antitumoral drugs for example doxorubicine, daunorubicin, cisplatinum, etc., have high toxicity, towards different organs, among which are stomach and intestine. Said toxicity is further worsened in the above mentioned pathologies of oxidative stress and/or endothelial dys unctions.
- Antidementia drugs for example nicotine and colino- mimetics, are characterized by a poor tolerability especially in the above mentioned pathologies.
- An object of the invention are compounds or their salts having the following general formulas (I) and (II):
- X O, S, NR 1C , R lc is H or a linear or branched alkyl, having from 1 to 5 carbon atoms, or a free valence
- T B and T BI are equal or different
- X is a bivalent bridging bond as defined below;
- C is the bivalent -T c -Y- radical, wherein
- X being as above defined;
- Y is an alkylenoxy group R'O wherein R' is linear or branched when possible C--C 20 . preferably having from 1 to
- nIX is an integer between 0 and 3, preferably 1
- nllX is an integer between 1 and 3, preferably 1;
- Rpjxf R ⁇ x ' ' ⁇ TIIX ' ⁇ IIX ' ' e ⁇ - u l to or different from each other are H or a linear or branched C- ⁇ - ⁇ alkyl; prefe ⁇
- Y 3 is a saturated, unsaturated or aromatic heterocyclic ring containing at least one nitrogen atom, preferably one or two nitrogen atoms, said ring having 5 or 6 atoms.
- n3 is an integer from 0 to 3 and n3 ' is an integer from 1 to 3 ;
- nf ' is an integer from 1 to 6 preferably from 1 to 4 ;
- R lf H, CH 3 and nf is an integer from 1 to
- T CI and T CII are equal or different
- Y' is as Y above defined, but with three free valences instead of two, preferably: a -R'O- group wherein R' is as above defined, I preferably from 1 to 6 carbon atoms, most preferably 2 - 4 , or
- n3 is an integer from 0 to 3 and n3 ' is an integer from 1 to 3;
- n3 and n3 ' have the above mentioned meaning
- nf ' is an integer from 1 to 6 preferably from 1 to 4 ; wherein one hydrogen atom on one of the carbon atoms is substituted by a free valence; - ( CH - CH 2 - 0 ) nf -
- R lf H, CH 3 and nf is an integer from 1 to
- X 2 bivalent radical, is such that the corresponding precursor of B: -T B —X 2 —T BI - meets the test 4, precursor in which the T B and T BI free valence are each saturated with
- T B and/or T BI CO or X, in connection with the values of t, t', tx and txx;
- X 2a monovalent radical such that the corresponding precursor of ⁇ - -T BII —X 2a meets the test 4, precursor wherein the free valence of T BII is saturated with -OZ, -Z or with
- Z H or R la , R la being a linear or when possible branched C 1 -C 10 alkyl, preferably
- test 1 is a test in vivo carried out on four groups of rats (each formed by 10 rats), the controls (two groups) and the treated (two groups) of which one group of the controls and one group of the treated respectively are administered with one dose of 25 mg/kg s.c. of N-ethylmaleimide (NEM), the controls being treated with the carrier and the
- the drug can be used to prepare the compounds of general formula (I) and (II), when the group of rats treated with NEM + carrier + drug shows gastrointestinal damages, or in the group treated with NEM + carrier + drug are observed gastrointestinal damages greater than those of the group treated with the carrier, or of the group treated with the carrier + drug, or of the group treated with the carrier + NEM;
- test 2 CIP is a test in vitro wherein human endothelial cells from the umbilical vein are harvested under standard conditions, then divided into two groups (each group replicated five times), of which one is treated with a mixture of the drug 10 "4 M concentration in the culture medium, the other group with the carrier; then cumene hydroperoxide (CIP) having a 5 mM concentration in the culture medium is added to each of the two groups; the drug meets test 2, i.e.
- test 3 is a test in vivo carried out on four groups of rats (each group formed by 10 rats) for 4 weeks and receiving drinking water, the controls (two groups) and the treated (two groups), of which one group of the controls and of the treated respectively receives in the above 4 weeks drinking water added of N- ⁇ -nitro- L- arginine methyl ester (L-NAME) at a concentration of 400 mg/litre, the controls in the 4 weeks being administered with the carrier and the treated in the 4 weeks with the carrier + the drug, administering the carrier or the drug + carrier once a day, the drug being administered at the maximum dose tolerated by the group of rats not pretreated with L-NAME, i.e.
- the highest dose administrable to animals at which no manifest toxicity appears i.e. such as to be symptomatologically observable
- the water supply is stopped for 24 hours and then sacrified, determining the blood pressure 1 hour before sacrifice, and after sacrifice of the rats determining the plasma glutamic pyruvic transaminase (GPT) after sacrifice, and examining the gastric tissue; the drug meets test 3, i.e.
- the drug can be used to prepare the compounds of general formula (I) and (II), when in the group of rats treated with L-NAME + carrier + drug, greater hepatic damages (determined as higher values of GPT) and/or gastric and/or cardiovascular damages (determined as higher values of blood-pressure) are found in comparison in comparison respectively with the group treated with the carrier alone, or with the group treated with the carrier + drug, or with the group treated with the carrier + L-NAME; the precursors of B or B-_ with the free valences saturated as above defined must meet test 4: it is an analytical determination carried out by adding portions of methanol solutions of the precursor of E cr B at a 10 "4 M concentration, to a methanol solution of DPPH ( 2 , 2 -diphenyl- 1-picryl hydrazyl - free radical); after having maintained the solution at room temperature away from light for 30 minutes, it is read the absorbance at the wave length of 517 nm of the test solution and of a solution containing only DPPH in the same
- a s and A c are respectively the absorbance values of the solution containing the test compound + DPPH and that of the solution containing only DPPH; the precursor complies with test 4 when the percentage of inhibition as above defined is equal to or higher than 50%.
- precursor compound of B or B 1 precursor of
- the X 2 or X 2a radical in the formulas (I) and (II) respectively) is selected from the following classes of compounds: Aminoacids, selected from the following: L-carnosine (formula Cl ) , anserine (CII), selenocysteine (CIII), selenomethionine (CIV), penicilia-mine (CV), N-acetyl- penicillamine (CVI), cysteine (CVII), N-acetyl- cysteine (CVIII), glutathione (CIX) or its esters, preferably ethyl or isopropyl ester:
- Aminoacids selected from the following: L-carnosine (formula Cl ) , anserine (CII), selenocysteine (CIII), selenomethionine (CIV), penicilia-mine (CV), N-acetyl- penicillamine (CVI), cysteine (CVII), N
- hydroxyacids selected from the following: gallic acid (formula DI ) , ferulic acid (DH), gentisic acid (Dili), citric acid (DIV), caffeic acid (DV), hydro caffeic acid (DVI), p-coumaric acid (DVII), vanillic
- Aromatic and heterocyclic mono- and polyalcohols selected from the following: nordihydroguaiaretic acid (El), quercetin (EH), catechin (EIII), ka- empferol (EIV), sulphurethyne (EV), ascorbic acid (E- VI), isoascorbic acid (EVII), hydroquinone (EVIII), gossypol (EIX) , reductic acid (EX), methoxy- hydroquinone (EXI), hydroxyhydroquinone (EXII), propyl gallate (EXIII), saccharose (EXIV), vitamin E (EXV), vitamin A ( EXVI ) , 8-quinolol (EXVII), 3- ter-butyl-4-hydroxyanisole (EXVIII), 3 -hydroxyflavone (EXIX), 3,5-ter-butyl-p-hydroxytoluene (EXX), p-ter- buty
- EXXXV aromatic and heterocyclic amines, selected from the following: N, N' -diphenyl -p-phenylenediamine (Ml), ethoxyquin (Mil), thionine (Mill), hydroxyurea (M-
- NI fumaric acid
- Nil dihydroxymaleic acid
- NIV thioctic acid
- NV edetic acid
- NVI bilirubin
- 3 -methylendioxycinna ic acid
- NVIII piperonylic acid
- Tests 1-3 that are carried out for selecting the precursor drug (hereafter indicated in the tests also as “drug”) to be used for the synthesis of the products of the invention are in details the following:
- Test 1 evaluation of the gastrointestinal damage from oxidative stress induced by free radicals formed following administration of N-ethylmaleimide (NEM) (H.G. Utley, F. Bernheim, P. Hochstein "Effects of sulphydril reagents on pe- roxidation in microsomes" Archiv. Biochem. Biophys. 118, 29-32 1967).
- mice are distributed in the following groups (no. 10 animals for group) :
- A) Control groups are distributed in the following groups (no. 10 animals for group) :
- treatment only carrier (aqueous suspension 1% w/v of carboxymethylcellulose , dose: 5 ml/Kg when the drug is administered by os, or a physiologic solution when parenterally administered, i.e. by subcutaneous , intraperitoneal, intravenous or intermuscular route) ,
- the administration routes are those known for the drug, and can be the oral or subcutaneous , intraperitoneal , intravenous or intramuscular route .
- the NEM dose is of 25 mg/kg in physiologic solution (sub cutaneous route) and the drug is administered one hour later, in suspension in the carrier, as a single dose which corresponds to the maximum one, or the highest still tolerated by the animals of the group of rats not pretreated with NEM, i.e. the highest administrable dose to said group at which there is no manifest toxicity in the animals, defined as a toxicity that is clearly recognizable for its symptoms.
- the animals are sacrificed after 24 hours and then one proceeds to the evaluation of the damage to the gastrointestinal mucosa.
- the drug meets test 1, i.e. it can be used to prepare the compounds of general formula (I) and (II), when the group of rats treated with NEM + carrier + drug shows gastrointestinal damages, or in said group the gastrointestinal damages noticed are greater than those shown by the group treated with the carrier alone, or the group treated with carrier + drug, or the group treated with carrier + NEM, even though the drug pharmacotherapeutic efficacy, assayed by using specific tests, is not significantly reduced.
- CIP Protection parameter of endothelial cell against the oxidative stress induced by cumene hydroperoxide
- Human endothelial cells of the umbilical vein are prepared according to an usual standard procedure. Fresh umbilical veins are filled with a 0.1% by weight collagenase solution and incubated at 37°C for 5 minutes.
- the veins are perfused with medium M 199 (GIBCO, Grand Island, NY) pH 7.4 further added of other substances, as described in the examples.
- the cells are collected from the perfusate by centrifugation and harvested in culture flasks T-75, pretreated with human fibronectin. The cells are then harvested in the same medium, further added with 10 ng/ml of bovine hypothalamic growth factor.
- the cells of the primary cell culture i.e. that directly obtained from ex-vivo
- the culture is stopped and the layers washed and trypsinized.
- the cellular suspensions are transferred into the wells of a cell culture plate having 24 wells , half of which is then additioned with the same culture medium containing the drug at a 10 "4 M concentration, and harvested in a thermostat at 37°C at a constant moisture. Only the cells coming from said first sub-cultures are used for the experiments with cumene hydroperoxide (CIP).
- CIP cumene hydroperoxide
- the cells are identified as endothelial cells by morphological examination and by their specific immunological reaction towards factor VIII; said cultures did not show any contaminations from myocytes or fibroblasts.
- the cellular culture medium is removed and the cellular layers are carefully washed with a physiologic solution at a temperature of 37°C.
- the wells of the culture plate are then incubated for one hour with CIP at a 5 mM concentration in the culture medium.
- the evaluation of cellular damage is carried out by determining the per cent variation of the DNA fragmentation with respect to the control group (treated with CIP alone), evaluating the fluorescence variation at the wave length of 405-450 nm. 5 replicates for each sample are carried out .
- the drug meets the test, i.e. it can be used for preparing the compounds of general formula (I) and (II), when a statistically significant inhibition of apoptosis (cellular damage) induced by CIP with respect to the group treated with CIP alone is not obtained at p ⁇ 0.01.
- Test 3 evaluation of the endothelial dysfunction induced by administration of L-NAME (N -nitro-L- arginine -methyl ester) J. Clin. Investigation 90, 278-281,1992.
- the endothelial dysfunction is evaluated by determining the damage to the gastrointestinal mucosa, the hepatic damage and blood hypertension induced by administration of L-NAME.
- the animals are divided in groups as herein below shown.
- the group receiving L-NAME is treated for 4 weeks with said compound dissolved at a concentration of 400 mg/litre in drinking water.
- the following groups are constituted (No. 10 animals for group) :
- the administration routes are those known for the drug, and can be the oral or subcutaneous , intraperiteneal , intravenous or intramuscular route .
- the drug is administered at that dose which results the highest still tolerated by the animals of the group of rats not pretreated with L-NAME, i.e. the highest administrable dose at which there is no evident toxicity in the animals, i.e a toxicity recognizable for its symptoms.
- the drug is administered once a day for 4 weeks .
- a blood pressure increase is taken as an evaluation of the damage to vascular endothelium.
- the damage to the gastric mucosa is evaluated as illustrated in test 1 (see example Fl ) .
- the hepatic damage is determined by evaluation of the glutamic -pyruvic transaminase (GPT increase) after sacrifice.
- the drug meets test 3, i.e. it can be used for preparing the compounds of general formula (I) and (II), when in the group of rats treated with L-NAME + drug + carrier it is found an higher hepatic damage (GPT) and/or an higher gastric damage and/or an higher cardiovascular (blood-pressure ) damage in comparison to that of the group treated with the carrier alone, or of the group treated with carrier + drug, or of the group treated with carrier + L-NAME; even if the drug pharmaco- therapeutic efficacy, assayed by specific tests, is not significantly reduced.
- GPT hepatic damage
- gastric damage and/or an higher cardiovascular (blood-pressure ) damage
- blood-pressure blood-pressure
- Test 4 is a colorimetric test which affords to establish whether the precursor of B or B 1 (precursor of the X 2 or X 2a of the formulas (I) and (II) respectively), inhibits the production of radicals from DPPH ( 2 , 2 -diphenyl- 1 - icryl-hydrazyl ) (M.S. Nenseter et Al . , Atheroscler. Throm . 15, 1338- 1344, 1995). 100 ⁇ M solutions in methanol of the tested substances are prepared, and an aliquot of each of said solutions is added to a DPPH solution in methanol 0.1 M.
- a s and A c are respectively the absorbance values of the solution containing the test compound together with DPPH and of the solution containing only DPPH.
- the B or B-L precursor satisfies test 4 if their effectiveness in inhibiting radical production as above defined, is equal to or higher than 50% at the indicated concentration (10 "4 M) .
- the products of the invention of the formulas are identical to or higher than 50% at the indicated concentration (10 "4 M) .
- Test 1 precursor drug: indomethacin
- the group of rats treated with NEM + indomethacin at the above mentioned dose shows gastrointestinal damages.
- Indomethacin can therefore be used as a drug for preparing the compounds (I) and (II) of the present invention.
- Test 2 precursor drugs: indomethacin, paracetamol and mesala- mine
- Indomethacin and paracetamol meet test 2 since the cellular damage (apoptosis) inhibition induced by CIP is not significantly different with respect to that of the controls.
- the above drugs can be used as drugs for preparing the compounds (I) and (II) of the present invention.
- mesalamine does not meet test 2, since it inhibits the apoptosis induced by CIP. Therefore mesalamine according to test 2 could not be used as a precursor to prepare the compounds (I) and (II) cf the present invention. It has been however found that mesalairiine submitted to test 1 causes gastrointestinal damages .
- mesalamine can be used as a precursor for preparing the compounds (I) and (II) of the present invention.
- Test 3 (L-NAME) precursor drugs paracetamol, simvastatin, omeprazole
- Paracetamol and simvastatin meet test 3 since they cause gastric and hepatic damages greater than those induced both by L-NAME + carrier and by the drug + carrier.
- omeprazole neither causes gastric nor hepatic damages, nor influences blood- pressure. According to test 3 omeprazole could not be used as a precursor for preparing the compounds (I) and (II) of the present invention.
- Test 4 (test for the precursor of B and B 1 used as bivalent linking bridge): precursor N-acetylcysteine
- N-acetylcysteine inhibits of 100% the production of radicals induced by DPPH, therefore it meets test 4. Therefore it can be used as precursor of B or B 1 .
- Y 3 is preferably selected from the following:
- Y is Y12 (pyridyl) substituted in positions 2 and 6.
- the bonds car- also be in asymmetric position, for example Y12 (pyridyl) car- be substituted also in position 2 and 3;
- Yl (pyrazcl) may be 3 , 5 -di ⁇ ub ⁇ tituted.
- the compounds according to the present invention of formula (I) and (II) can be transformed into the corresponding salts.
- the salts is the following: when in the molecule one nitrogen atom sufficiently basic to be saiified, in organic solvent such as for example acetonitrile, tetrahydrofuran, is present, it is reacted with an equimolecular amount of the corresponding organic or inorganic acid.
- organic solvent such as for example acetonitrile, tetrahydrofuran
- compounds Y or Y' of formula (III) is present.
- organic acids examples include oxalic, tartaric, maleic, succinic, citric acids.
- inorganic acids are: nitric, hydrochloric, sulphuric, phosphoric acids.
- the derivatives according to the invention can be used in the therapeutic indications cf the precursor drug, allowing to obtain the advantages exemplified hereinafter for some groups ese drugs :
- Anti- inflammatory drugs NSAIDs the invention compounds result very well tolerated and effective, even when the organism is debilitated and is under conditions of oxidative stress. Said drugs can be used also in those pathologies wherein inflammation plays a significant pathogenetic role, such as for instance, but not limited to, in cancer, asthma, miocardic infarction.
- Adrenergic blockers, of cc- or 3-blocker type the action spectrum of the compounds of formula (I) and (II) results wider than that of the starting drugs; to a direct action on the smooth musculature the inhibition of the nervous beta-adrenergic signals governing the contraction of the hematic vessels is associated. The side effects (dyspnoea, bronchoconstriction) affecting the respiratory apparatus are lower .
- Antithrombotic drugs the antiplatelet activity is potentiated and in the case of the aspirin derivatives the gastric tolerability is improved.
- Bronchodilators and drugs active on the cholinergic system the side effects affecting the cardio-vascular apparatus (tachycardia, hypertension) result lowered.
- Expectorants and mucolytic drugs the gastrointestinal tolerability results improved.
- Diphosphonates the toxicity relating to the ga ⁇ trointe- stinal tract is drastically lowered.
- Phosphodie ⁇ tera ⁇ e (PDE) (bronchodilator ⁇ ) inhibitors the therapeutic efficacy is improved, the dosage being equal; it is therefore possible, using the compounds of the invention to administer a lower dose of the drug and reduce the side effects.
- Anti leukotrienic drugs better efficacy.
- ACE inhibitor ⁇ better therapeutic efficacy and lower side effects (dyspnoea, cough) affecting the respiratory apparatus .
- Antidiabetic drugs insulin- sensitizing and hypoglycaemizing antibiotic, antiviral, antitumoral, anticolitic drugs, drugs for the dementia therapy: better efficacy and/or tolerability.
- the drugs which can be used as precursors in formulas (I) and (II) of the compounds of the invention are all those meeting at least one of the above mentioned tests 1, 2, 3.
- Examples of precursor drugs which can be used are the following:
- anti -inflammatory drugs aceclofenac, acemetacin, acetylsali- cylic acid, 5-amino-acetylsalicylic acid, alclofenac, al i- noprofen, amfenac, bendazac, bermoprofen, ⁇ -bisabolol, bromfe- nac, bromosaligenin, bucloxic acid, butibufen, carprofen, cinmetacin, clidanac, clopirac, diclofenac sodium, diflunisal, ditazol , enfenamic acid, etodolac, etofenamate, felbinac, fenbufen, fenclozic acid, fendosal, fenoprofen, fentiazac, fepradinol, flufenamic
- fortimicins gentamicin, micronomicin, neomycin, netilmicin, paromo ycin, ribo ⁇ tarrycin, sisomicin, spectinomycin, streptomici , tobrarrycin, tro ⁇ pectomycin; baca piciliir-, cefcape ⁇ e pivoxil, cefpodoxime proxetil, paniper.e , pivampiciilin, pivcefaiexin, sultamicillin, talampicillir.
- the preferred substances are the following: among anti-inflammatories : acetylsalicylic acid, 5- aminoacetyl ⁇ alicylic acid, carprofen, diclofenac sodium, diflu- nisal, etodolac, flufenamic acid, flunixin, flurbiprofen, ibuprofen, indomethacin, indoprofen, ketoprofen, ketorolac , lornoxicam, loxoprof ⁇ n, meclofenamic acid, m ⁇ f ⁇ namic acid, m ⁇ loxicam, mesalamine, naproxen, niflumic acid, olsalazine, piroxicam, sal ⁇ alate, ⁇ ulindac, ⁇ uprofen, tenoxicam, tiaprofenic acid, tolfena ic acid, tolmetin, zom ⁇ pirac, to oxi- prol ; among an
- ACE- inhibitors captoprii, enalapril, li ⁇ inopril, lo ⁇ artan, ramipril ;
- Beta blockers aiprenoiol, atenoiol, bupranolol , lab ⁇ talol, metipranolcl , metoprolol, pindolol, prcpranolol, timolol; an ithrombotic and vasoactive drugs: acetylsalicylic acid, ac ⁇ torphan, argatroban, clopidogrei, aiteparin, dipyridamole , enoxaparin, heparin, iiopro ⁇ t, midodrine, ozagrel, phenyipropanolar.ine , trifusal ; antidiabetic drugs: tclrestat , nicotinamide ; among antitumor drugs: anthrarr.ycin, da norubicin, doxorubicin, epirubicin, fluorouracyl , methotrexate, vinbla ⁇ tine; among
- Th ⁇ above mentioned substances, precursor drug ⁇ , are prepared according to the methods known in the prior art. S ⁇ for example in “The Merck Index, 12a Ed. (1996), herein incorporated by ref ⁇ r ⁇ nce. When available, the corresponding isomers, compri ⁇ ing optical i ⁇ om ⁇ r ⁇ , can b ⁇ us ⁇ d.
- Tomoxiprol is obtain ⁇ d according to th ⁇ m ⁇ thod d ⁇ scrib ⁇ id in EP 12,866.
- Th ⁇ choic ⁇ of the reactions for ⁇ ach method depends on the reactive groups pre ⁇ nt in th ⁇ precur ⁇ or drug molecule, in the precursor compound of B or B 1 , which can be, as above mentioned, bivalent or monovalent, and in th ⁇ precursor compound of C.
- the reactions are carried out with methods well known in the prior art, which allow to obtain bonds among the precursor drug, th ⁇ pr ⁇ cur ⁇ or drug of B cr B- and the precursor compound of C a ⁇ above defin ⁇ d.
- th ⁇ precur ⁇ or drug for example -COOH, -OH
- a covalent bond for example of e ⁇ t ⁇ r, amide, ether type
- said function can be restor ⁇ d with th ⁇ m ⁇ thods well known i the prior art.
- COOH and/or HX are pre ⁇ ent , they must be protect ⁇ d b ⁇ for ⁇ th ⁇ reaction according to the methods known in the art; for example as described -in the volume by Th. W. Greene : “Protective groups in organic synthe ⁇ i ⁇ ", Harward University Press, 1980.
- Th ⁇ RCOHal acylhalide is prepar ⁇ d according to the methods known in th ⁇ prior art, for example by thionyl or oxalyl chloride, p 111 or P v halide ⁇ in inert solvent under the reaction condition ⁇ , ⁇ uch as for example toluene, chloroform, DMF, etc.
- the pr ⁇ cursor drug of formula R- COOH is first converted into the corresponding acyl halid ⁇ RCOHal, as above mentioned, and then reacted with th ⁇ HX group of the precursor compound of B in the presence of an organic ba ⁇ e, ⁇ uch as triethylamine, pyridine, etc. using an in ⁇ rt solv ⁇ nt in th ⁇ r ⁇ action conditions such as toluen ⁇ , t ⁇ trahydrofuran, etc. at a temperature in the range 0°C-25°C.
- the precursor drug of formula R-COOH can be treated with an agent activating the carboxyl group selected from N,N' -carbonyldii- midazol (CDl), N-hydroxybenzotriazol and dicycloh ⁇ xylcar- bodiimide in solvent such as for example DMF, THF, chlo- roform ⁇ tc. at a temperature in the range -5°C-50°C and the obtained commpound react ⁇ d in ⁇ itu with th ⁇ reactive function of the precur ⁇ or compound of B for obtaining th ⁇ compound of formula (IA.l).
- an agent activating the carboxyl group selected from N,N' -carbonyldii- midazol (CDl), N-hydroxybenzotriazol and dicycloh ⁇ xylcar- bodiimide in solvent such as for example DMF, THF, chlo- roform ⁇ tc. at a temperature in the range -5°C-50°C and the obtained commpound react
- Th ⁇ ⁇ cheme i ⁇ the following:
- the acid can be converted into the corresponding sodic salt and then one can follow the known prior art methods for preparing the final compound, for example according to one of the following ⁇ ynthe ⁇ i ⁇ schemes :
- ⁇ , T 3 , X 2 , T BI , T c are as above defined, R 4 is selected from Cl, Br, Y is as above defined, X 1 is the Y radical fr ⁇ from th ⁇ oxyg ⁇ n atom, R 3 is Cl , Br, Iodin ⁇ ,
- R 3 OH th ⁇ compound of formula (lA.lb) is subje- ct ⁇ d to halog ⁇ nation, for example with PBr 3 , PC1 5 , S0C1 2 ,
- the two functional groups pres ⁇ nt on the precursor compound of B can be the following: lb.l A carboxylic group, which reacts with the HX function of the drug precursor, and a HX group, the latter reactive group of the pr ⁇ cursor compound of B b ⁇ ing ⁇ qual to or diff ⁇ r ⁇ nt from th ⁇ functional group of th ⁇ drug precursor.
- Th ⁇ formula of the precursor compound of B i ⁇ of the H-X-X 2 -COOH type, wherein X and X 2 are a ⁇ above defined.
- the H-X- function of the precursor compound of B is protected according to the known prior art methods and the carboxyl group is reacted, as above mentioned, according to the following ⁇ cheme:
- th ⁇ (1B.1) compound is r ⁇ acted with an halogenacid of formula Hal-X 1 - COOH which has b ⁇ n tr ⁇ at ⁇ d as pr ⁇ viously d ⁇ scrib ⁇ d in paragraph la.l, or with the corresponding halogenacid chloride.
- the compound (IIA.l) can be obtained with the known method of th ⁇ prior art.
- X NH
- it can be obtained from th ⁇ corresponding hydroxy-aminoacid , protecting the a inic group by the corresponding ter-bu- tyloxycarbonyl derivative and transforming the hydroxyl function into halogen group as described for the halogenation of the compound (lA.lb) in 2a.1.
- X- ' being as above d ⁇ fin ⁇ d, said compound being prepared from the corresponding hydroxy-diacid as describ ⁇ d for th ⁇ halog ⁇ nation of the compound (lA.lb) in 2a.1.
- the halog ⁇ ndiacid compound is tr ⁇ at ⁇ d with an ⁇ quimolar amount of an ag ⁇ nt activating the carboxyl group, under the conditions pr ⁇ viously described in la.l., and then it is reacted with the reactiv ⁇ function of the drug precursor mol ⁇ cul ⁇ .
- the second carboxylic function is treated with an activating agent, as previously made for the first, and react ⁇ d with th ⁇ pr ⁇ cursor compound of B 1 according to th ⁇ following scheme :
- the halogen atom is then ⁇ ub ⁇ tituted with th ⁇ ON0 2 group as abov ⁇ m ⁇ ntioned.
- the general ⁇ chem ⁇ is the following: R-T 1 -T B -X 2 -T BI -T c -X 1 -OH + NaN0 2 ⁇ A-B-C-NO a.2 If the compound obtained at the end of step A in la .2 has formula (IA.2) th ⁇ corr ⁇ ponding nitro ⁇ o derivative i ⁇ obtained treating an hydroxyacid of formula HO-X- ⁇ COOH, X ⁇ being as above defined, first with an agent activating the carboxyl group, a ⁇ de ⁇ crib ⁇ d in la.l, then reacting it with 1A.2 and the resulting product with sodium nitrite as d ⁇ scrib ⁇ d in 3a.1.
- th ⁇ compound (1B.1) is reacted with an hydroxyacid as d ⁇ scrib ⁇ d in 3a.2.
- the daily admini ⁇ trable do ⁇ are tho ⁇ e of the precur ⁇ or drugs, or in the case lower.
- the daily dose ⁇ can be found in the publication ⁇ of the field, ⁇ uch a ⁇ for example in "Phy ⁇ i- cian's Desk reference” .
- the precursor is naproxene (Formula VI), the precur ⁇ or of B i ⁇ N-ac ⁇ tylcisteine (formula CVIII)
- the organic phase is anhydrified with sodium sulphate and then evaporated at reduced pressur ⁇ . Th ⁇ obtain ⁇ d residue is purified by chromatography on silica gel eluting with ethyl acetate. 11.66 g of the expected product in the form of a white solid .p. 122°-126°C, is obtained.
- Th ⁇ pr ⁇ cursor is ibuprofen (Formula VII)
- the precur ⁇ or of B is N-acetylcistein ⁇ (formula CVIII)
- the reaction mixtur ⁇ is washed with HCl 5%, then with water and lastly with brine.
- the organic phas ⁇ is anhydrifi ⁇ d with sodium sulphat ⁇ and then evaporat ⁇ d at r ⁇ duced pressure.
- the obtained r ⁇ sidu ⁇ i ⁇ purifi ⁇ d by chromatography on ⁇ ilica gel eluting with ethyl acetat ⁇ . 13.3 g of the exp ⁇ ct ⁇ d product in the form of an oil ar ⁇ obtain ⁇ d.
- Th ⁇ precur ⁇ or i ⁇ indomethacin (Formula VIII), the precur ⁇ or of B is N-acetylcist ⁇ ine (formula CVIII)
- the obtained residu ⁇ is purified by chromatography on silica gel eluting with ethyl acetat ⁇ . 7.79 g of th ⁇ expected product in the form of a yellow solid m.p. 129°C, are obtained.
- the reaction mixture is left under stirring for 20 hours at room temperature, then it is diluted with ethyl ether and washed with water. After the organic phase has been anhydrified with sodium sulphat ⁇ , th ⁇ solv ⁇ nt is removed by evaporation at reduced pressure. The obtained crude product is purified by chromatography on silica gel, eluting with cycloh ⁇ xane/ ⁇ thyl acetate 1/1. 1.7 g of the ester in the form of a yellow solid with m.p. 130°-134°C are obtained.
- Th ⁇ precursor is flurbiprofen (Formula IX)
- the precursor of B is N-acetylcist ⁇ ine (formula CVIII)
- NCX 2131 compound is synth ⁇ tiz ⁇ d according to the proce ⁇ s describ ⁇ d in Exampl ⁇ 1.
- the precursor is ibuprofen (Formula VII), the precursor of B i ⁇ f ⁇ rulic acid (formula DH)
- the obtained residu ⁇ is purified by chromatography on silica gel, eluting with ethyl acetate/n-hexane 7/3. 5.1 g of
- the obtained residu ⁇ is purified by chromatography on ⁇ ilica gel eluting with n- hexane/ethyl acetate 8/2.
- NCX 2216 compound is synthetized according to the proce ⁇ s described in Example 5.
- the total proces ⁇ yield is 32%.
- NCX 2160 wherein the precursor is acetaminof ⁇ n (parac ⁇ tamol) having formula (X) and the precur ⁇ or of B i ⁇ (L) -carno ⁇ ine (NCX 2053) having formula ( Cl ) :
- N- ( 4 -bromobutyryl ) -3-alanyl (L) -histidine (3 g, 8 mmoles) in chloroform (50 ml) and N,N-dim ⁇ thylformamid ⁇ (4 ml), parac ⁇ tamol (1.21 g, 8 mmoles), N,N-dicyclohexyl carbodiimide (1.65 g, 8 mmoles) and dimethylaminopyridine (0.04 g, 0.36 mmoles) are added under stirring.
- the mixture i ⁇ let react at room temperature for 6 hour ⁇ .
- pr ⁇ cursor ambroxol having formula (XII) and the pr ⁇ cursor of B is r ⁇ presented by ferulic acid having formula (DH):
- the reaction mixture is concentrated under vacuum, tr ⁇ at ⁇ d with methylen chloride, washed with a HCl 1% solution and then with water.
- the obtained residu ⁇ is purified by chromatography on silica g ⁇ l, ⁇ luting with n-h ⁇ xan ⁇ /ethyl acetate 1/1.
- the organic solution is evaporat ⁇ d at r ⁇ duc ⁇ d pressure.
- the obtained residue is purified by chromatography on ⁇ ilica gel eluting with n-hexane/ethyl acetate 7/3.
- NCX 2211 wherein the precursor is al ⁇ ndronic acid of formula (XIII) and th ⁇ pr ⁇ cursor of B i ⁇ th ⁇ f ⁇ rulic acid (formula DH ) :
- Th ⁇ compound i ⁇ pr ⁇ par ⁇ d according to th ⁇ procedure reported in Example 1, by using N- ter -butoxycarbonyl -p ⁇ nicillamin ⁇ inst ⁇ ad of N-acetyl ci ⁇ teine.
- b) Synthe ⁇ i ⁇ ofS-[[2-[4-[(4 -chlorophenyl ) phenylm ⁇ thyl ] - 1-pipe- razinyl ] ethoxy ] acetyl ] -peniciila in ⁇ - 4 - (nitroxy )butyl e ⁇ ter .
- Th ⁇ compound i ⁇ obtain ⁇ d from the previous one by following the proc ⁇ dur ⁇ d ⁇ scrib ⁇ d in st ⁇ p e) of Example 9 to remove the protectiv ⁇ group N- t ⁇ r-butoxycarbonyl and r ⁇ cov ⁇ r th ⁇ aminic function. Yi ⁇ ld: 26%.
- NCX 2134 wherein the precursor is enalapril of formula (XV) and th ⁇ pre- cursor of a i ⁇ -acetylci ⁇ teine (formula CV ⁇ H
- Tne corr is syr.th- .oilowing the procedure repor ec n ---xamo--.. Yi ⁇ ld: 27
- Th ⁇ final compound is obtained by hydrolizing the bond between the aminic function and th ⁇ N- ter-butoxycarbonyl protective group as describ ⁇ d in Exampl ⁇ 9, ⁇ t ⁇ p e). Yield ⁇ : 28%.
- precur ⁇ or is tacrin ⁇ of formula (XX) and th ⁇ pr ⁇ cursor of B is th ⁇ f ⁇ rulic acid (formula DH):
- the animals are kept und ⁇ r obs ⁇ rvation for 14 days.
- toxic symptoms app ⁇ ared, ev ⁇ n after administration of a 100 mg/Kg dose.
- Test 1 exp ⁇ rim ⁇ ntal model in vivo with N-ethylmal ⁇ imide (NEM) : study of the gastric tol ⁇ rability of ⁇ om ⁇ drug ⁇ ⁇ cr ⁇ n ⁇ d as precursors of the compounds of the inv ⁇ ntion.
- NEM N-ethylmal ⁇ imide
- the animal ⁇ (rat ⁇ , weight about 200 g) are di ⁇ tributed in the following group ⁇ (No. 10 animal ⁇ for group):
- the drugs assayed in this experim ⁇ nt are the following (Table I): indomethacin, ambroxol, mesalamine, sodic alendro- nate, tacrine, omeprazol, misoprostol.
- the maximum tolerated dose determined by administering each substance by the above said routes to th ⁇ animals not treated with NEM, is report ⁇ d in Table I. With higher do ⁇ es than, those reported in the Table, ent ⁇ ropathy, diarrho ⁇ a, d ⁇ pr ⁇ ion, tr ⁇ mor and s ⁇ dation hav ⁇ app ⁇ ar ⁇ d in th ⁇ animals.
- All the rat ⁇ of group II showed gastric lesions after administration with the following drugs: indomethacin, ambroxol, mesalamine, sodic alendronat ⁇ , tacrine.
- Said drugs ther ⁇ fore can be used in the ⁇ ynthesis of the products of the invention.
- Test 2 inhibition of apoptosi ⁇ (DNA fragmentation) induced in th ⁇ ⁇ ndoth ⁇ lial cells by CIP in the pres ⁇ nce of some drugs scr ⁇ ened a ⁇ precur ⁇ or ⁇ of th ⁇ compounds of the invention.
- precur ⁇ or drugs Table II: indomethacin, paracetamol, clopidogrel, salbutamol, ambroxol, sodic al ⁇ n- dronat ⁇ , diphyllin ⁇ , c ⁇ tirizine, enalapril, nicotinamide, ampicilline, aciclovir, mesalamine, tacrine, simvastine, omeprazol have be ⁇ n t ⁇ t ⁇ d .
- Human ⁇ ndoth ⁇ lial cells of the umbilical vein ar ⁇ prepared according to a standard method. Fr ⁇ sh umbilical veins are filled with a collagenas ⁇ solution 0.1% by w ⁇ ight and incubat ⁇ d at 37°C for 5 minut ⁇ s .
- vein ⁇ are perfu ⁇ d with the medium M 199 (GIBCO, Grand Island, NY) pH 7.4 with 0.1% (weight/volume) of collagenase, added with 10% of bovin ⁇ fetus serum (10 mcg/ml), sodium heparin (50 mcg/ml), thimidine (2.4 mcg/ml), glutamin ⁇ (230 mcg/ml), p ⁇ nicillin (100 Ul/ml), streptomycin (100 mcg/ml) and streptomycin B (0.125 mcg/ml).
- bovin ⁇ fetus serum 10 mcg/ml
- sodium heparin 50 mcg/ml
- thimidine 2.4 mcg/ml
- glutamin ⁇ 230 mcg/ml
- p ⁇ nicillin 100 Ul/ml
- streptomycin 100 mcg/ml
- streptomycin B (0.125 mcg/
- the cells are collect ⁇ d from th ⁇ perfusate by centrifugation at 800 rpm and harvested in culture fla ⁇ k ⁇ T-75, pretreated with human fibronectin. C ⁇ lls are then harvested in the same medium, added with bovine hypothalamic growth factor (100 ng/ml).
- bovine hypothalamic growth factor 100 ng/ml.
- the drug is not soluble in th ⁇ cultur ⁇ m ⁇ dium, it i ⁇ form ⁇ rly dissolv ⁇ d in a ⁇ mall amount of di- methylsulphoxide.
- Th ⁇ maximum amount of dim ⁇ thylsulphoxid ⁇ which can be added to th ⁇ culture medium i ⁇ 0.5%.
- the cellular culture medium is removed and the cellular layers ar ⁇ carefully washed with a standard physiologic solution buffered with phosphate 0.1 M pH 7.0, at th ⁇ temperature of 37°C. The content of each well is then incubated for one hour with a CIP suspension in the culture medium at a 5 mM concentration. Evaluation of the cellular damage (apoptosis) is carried out by determining the per cent variation of the DNA fragmentation in the cultures containing the drug + CIP with respect to the controls treated with CIP only.
- Results are given in Table II and show that indomethacin, paracetamol, clopidogrel, ⁇ albutamol , ⁇ odic alendronate, diphyllin ⁇ , c ⁇ tirizin ⁇ , enalapril, nicotinamide, ampicilline, aciclovir, tacrine, omeprazol do not ⁇ ignificantly inhibit apoptosis; these drugs can ther ⁇ fore be used for preparing the products of the invention.
- Test 3 experimental in vivo model with N w -nitro-L-arginine- methyl ester (L-NAME): gastric tolerability (gastrointestinal damage incidence), hepatic (GPT dosage, glutamic -pyruvic transaminase) and cardiovascular (blood pressure) tolerability of some drugs screened as precursors of the compounds of the invention.
- L-NAME N w -nitro-L-arginine- methyl ester
- Th ⁇ ⁇ ndoth ⁇ lial dy ⁇ function i ⁇ evaluated by determining the damage induced by L-NAME admini ⁇ tration to the ga ⁇ trointe ⁇ tinal mucosa, the hepatic damage (GPT increase), and the vascular endoth ⁇ lium or cardiova ⁇ cular damag ⁇ as blood hyp ⁇ rt ⁇ nsion .
- Th ⁇ animal ⁇ (rat ⁇ , average weight 200 g) are divided in groups as h ⁇ r ⁇ in below de ⁇ cribed.
- the group rec ⁇ iving L-NAME is tr ⁇ ated for 4 we ⁇ ks with ⁇ aid compound di ⁇ solv ⁇ d at th ⁇ conc ⁇ ntration of 400 mg/litr ⁇ in drinking wat ⁇ r.
- Th ⁇ following groups (No. 10 animals for group) ar ⁇ con ⁇ titut ⁇ d:
- tr ⁇ atm ⁇ nt only carrier ( aqueous suspension 1% w/v of carboxymethylcellulose, do ⁇ e: 5 ml/Kg wh ⁇ n th ⁇ drug i ⁇ admini ⁇ t ⁇ r ⁇ d by o ⁇ , physiologic solution wh ⁇ n by parenteral route),
- the drugs used in the test are paracetamol, doxorubicine, simvastatine, omeprazol and misoprostol. Each drug is administered once a day for 4 weeks.
- the maximum tolerated dose of the drug being administered to the animals is determined by evaluating, in a separate dose scaling up ⁇ xp ⁇ rim ⁇ nt on untr ⁇ ated animals, th ⁇ appearance in the animal ⁇ of symptoms such a ⁇ enteropathy, diarrhoea, depre ⁇ ion, tr ⁇ mor, s ⁇ dation.
- the damage to the gastric mucosa is evaluat ⁇ d as pr ⁇ viously m ⁇ ntion ⁇ d in t ⁇ st 1 ( ⁇ x. FI ) .
- Th ⁇ hepatic damage is determined by evaluation after the sacrific ⁇ of th ⁇ glutamic - pyruvic transaminase (GPT increas ⁇ ).
- the test result ⁇ are reported in Table IV.
- the % gastric lesions have been determined as in Test 1.
- the % GPT and % blood pressure values are ref ⁇ rred to the corresponding valu ⁇ found in th ⁇ animals of th ⁇ 1st group of th ⁇ control groups .
- the average value of the blood pressure in this group was of
- n 105 + 8 m Hg .
- Th ⁇ r ⁇ ult ⁇ obtain ⁇ d show that parac ⁇ tamol, doxorubicin and simva ⁇ tatin ⁇ cau ⁇ h ⁇ patic damag ⁇ and ga ⁇ tro ⁇ nteropathy (GPT values and th ⁇ gastric lesions are % high ⁇ r compar ⁇ d both with the corresponding groups treated with the drug, in th ⁇ ab ⁇ nce of L-NAME, and with the control ⁇ treat ⁇ d with L-NAME) .
- Th ⁇ e drug ⁇ can ther ⁇ for ⁇ b ⁇ us ⁇ d for pr ⁇ paring th ⁇ products of th ⁇ inv ⁇ ntion.
- Test 4 inhibition of the radical production from DPPH of some substances to be us ⁇ d a ⁇ pr ⁇ cur ⁇ or ⁇ of B or BI (r ⁇ f. Formula ⁇ I and II of th ⁇ invention)
- Solutions in methanol of the tested sub ⁇ tances at a final concentration 100 ⁇ M are initially prepar ⁇ d. 0.1 ml of ⁇ ach of these solutions are added to aliquots of 1 ml of a methanol solution 0.1 M of DPPH and th ⁇ n th ⁇ final volume is brought to 1.5 ml. After having stored the solutions at room temperature away from light for 30 minute ⁇ , the ab ⁇ orbance at the wave length of 517 nm is read. It is determined the absorbance decreas ⁇ with r ⁇ sp ⁇ ct to th ⁇ absorbanc ⁇ of a solution containing the same concentration of DPPH.
- Th ⁇ drugs w ⁇ r ⁇ administ ⁇ r ⁇ d by o ⁇ at the do ⁇ e of 10 mg/Kg, in carri ⁇ r carboxymethylcellulo ⁇ 1% in water, 5 ml/Kg.
- Th ⁇ drug ⁇ u ⁇ d in th ⁇ experiment are th ⁇ following: diclofenac and the corresponding thioest ⁇ r with ( 4 -nitroxy)bu- tyryl p ⁇ nicillamin ⁇ (Ex. 26), piroxicam and the corre ⁇ ponding ester with the p- ( 4 -nitroxy)butyryloxy- ferulic acid (Ex. 25), the acetylsalicylic acid and the corresponding thioester with N-acetyl- ( 4 -nitroxy)butyrylci ⁇ tein ⁇ (Ex. 24).
- the antiinflammatory activity is expre ⁇ d a ⁇ % inhibition of th ⁇ l ⁇ ucocyte infiltration with re ⁇ pect to the leucocyt ⁇ infiltration value found in the animal ⁇ treat ⁇ d with th ⁇ carrier and pretr ⁇ at ⁇ d with L-NAME, th ⁇ % inhibition of th ⁇ ga ⁇ troint ⁇ tinal damage wa ⁇ ⁇ valuat ⁇ d as previously d ⁇ crib ⁇ d in Test 1 (ex. 1), and th ⁇ % blood pressure was evaluated one hour befor ⁇ th ⁇ ⁇ acrific ⁇ and r ⁇ f ⁇ rr ⁇ d tc that of the l ⁇ t control group (treatm ⁇ nt: carrier). In this group of animals the average pres ⁇ ur ⁇ value wa ⁇ of 108 + 10 m Hg .
- Example F5 The te ⁇ t for gastrointestinal damage of Example F5 was repeated but omitting th ⁇ pretr ⁇ atment of animals with L-NAME.
- the t ⁇ sted drug ⁇ , th ⁇ r ⁇ of admini ⁇ tered do ⁇ and re ⁇ ult ⁇ are report ⁇ d in Tabl ⁇ VII. From th ⁇ Table it i ⁇ drawn that ga ⁇ tropathy incidence is much lower in the group ⁇ treat ⁇ d with th ⁇ compound ⁇ of th ⁇ invention in the confront of the group ⁇ treated with the corre ⁇ ponding precursors .
- the precursor is doxorubicin of formula (XXXII) and the precursor of B is ferulic acid of (formula DH )
- Example FI was r ⁇ p ⁇ at ⁇ d with four groups of rat ⁇ ( ⁇ ach group of of ten animal ⁇ ), all of them receiving NEM, and orally admini ⁇ ter ⁇ d a ⁇ it follows : a. control group : the vehicle formed of an aqueous su ⁇ p ⁇ nsion 1% w/v of carboxymethylcellulose , b. one group (group b - comparativ ⁇ ) administ ⁇ red at the same time with 5 mg/Kg (0.014 mmoles/Kg) of indom ⁇ thacin + 2.3 mg/Kg (0.014 mmoles/Kg) of N-acetylcy ⁇ teine in th ⁇ same above vehicl ⁇ , c.
- group d administer ⁇ d with 8,7 mg/Kg (0.014 mmol ⁇ s/Kg) of the indomethacin thioest ⁇ r with N-ac ⁇ tyl- (4- nitroxy)butyryl cisteine (r ⁇ f. Ex. 3), in th ⁇ abov ⁇ same vehicle.
- Test 4 Scre ⁇ ning of th ⁇ ⁇ ffectiven ⁇ ss of th ⁇ list ⁇ d compounds in inhibiting radical production from
Abstract
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-
2004
- 2004-12-30 US US11/024,857 patent/US7378412B2/en not_active Expired - Fee Related
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ITMI990753A1 (en) | 2000-10-13 |
IT1311924B1 (en) | 2002-03-20 |
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AU778989B2 (en) | 2004-12-23 |
US20050261242A1 (en) | 2005-11-24 |
JP2002541233A (en) | 2002-12-03 |
RU2237657C2 (en) | 2004-10-10 |
CA2370412A1 (en) | 2000-10-19 |
AU4400100A (en) | 2000-11-14 |
EP1169294B1 (en) | 2007-12-05 |
ATE380170T1 (en) | 2007-12-15 |
DE60037313D1 (en) | 2008-01-17 |
IL185264A0 (en) | 2008-02-09 |
HUP0203378A3 (en) | 2004-07-28 |
US7378412B2 (en) | 2008-05-27 |
NO20014927L (en) | 2001-12-13 |
KR20060122986A (en) | 2006-11-30 |
IL145601A0 (en) | 2002-06-30 |
CN1354740A (en) | 2002-06-19 |
BR0009702A (en) | 2002-01-08 |
CN1230416C (en) | 2005-12-07 |
EP1169294A2 (en) | 2002-01-09 |
KR20020005667A (en) | 2002-01-17 |
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NO20014927D0 (en) | 2001-10-10 |
DE60037313T2 (en) | 2008-11-27 |
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